The problem is that the alleys are not plowed in Chicago. I had an M4 with winters and you are stuck if you stop in the alley. You are essentially the plow plus after the first day of freezing, it is a sheet of ice underneath any snow. I gave up after 1 winter and bought an AWD SUV to complement my sports cars. But my Audi S5 with winters was a tank. If you have direct access to the streets from a garage, it is not that bad if you can avoid driving the few days a year with heavy snow.